


So How About That Date? (A Heist With Markiplier x Reader Collection [SFW])

by emptymasks



Category: A Heist With Markiplier, A Heist With Markiplier (Web Series), Markiplier (YouTube RPF), Who Killed Markiplier? (Web Series), markiplier - Fandom
Genre: A heist with Markiplier - Freeform, Comfort, Cuddling & Snuggling, Cute, Depression, Emotional Hurt/Comfort, Everyone Needs A Hug, F/M, Fluff, Fluff and Hurt/Comfort, Gender Dysphoria, Gender Identity, Gender-Neutral Pronouns, Genderfluid, Hugs, Hurt/Comfort, M/M, Markiplier - Freeform, Other, POV Second Person, Pet Names, Reader-Insert, References to Depression, Sleepy Cuddles, Talk of Prison, Tooth-Rotting Fluff, Touch-Starved, Trans Character, Trans Male Character, gender neutral reader, really wish there were proper tags for the heist boys, trans male! reader (in some chapters), trans! wilford
Language: English
Status: In-Progress
Published: 2019-10-31
Updated: 2019-11-20
Packaged: 2021-01-15 22:16:57
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 5,544
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21260525
Author URL: https://archiveofourown.org/users/emptymasks/pseuds/emptymasks
Summary: A collection of SFW fics, ficlets and drabbles for characters from A Heist With Markiplier.I'm open for requests/headcannons/prompts/ideas for this fic for (just comment on a chapter or send me an ask on tumblr @emptymasks):•Yancy x reader•Illinois x reader•Darkiplier x reader•Damien x reader•Heist! Mark x reader•Captain Magnum x reader•Wilford x readerReader is always gender-neutral unless it's important for the reader to be a certain gender (e.g. a character reaffirming a trans reader's gender).





	1. Yancy x Reader - Yancy comforting you

**Summary for the Chapter:**

> You heard a door open and panic set in as you wanted to move so you wouldn’t be seen in this state but your body felt so heavy, even just heaving yourself up onto the bed seemed impossible.
> 
> “Sweetheart, yous in here?”

You had thought today would be better. You’d been feeling better, you’d been feeling fine, joyful even, but then just one little thing tipped the late-stage jenga tower your mind was still in and you’ve fallen back further than you’d been in ages. You wished your mind would just be less sensitive, that it wouldn’t take some things so personally and seriously, that it wouldn’t take one little thing that someone said and use it to label you as a failure.

You were sat on the floor with your back against the side of your bed. For some reason being on the floor grounded you, the bed was too soft, too high up. Your breathing was ragged, but not too panicked yet, if you could just get yourself to calm down, or fuck if you needed to cry then could your body just cry already and get it out and over with. You scrubbed your hands around your dampening eyes and sank further into yourself.

You heard a door open and panic set in as you wanted to move so you wouldn’t be seen in this state but your body felt so heavy, even just heaving yourself up onto the bed seemed impossible.

“Sweetheart, yous in here?” Yancy’s voice called out from beyond the bedroom and you don’t think you could have called back even if you wanted to. “Not answering me huh, what kind of game is yous…?” The bedroom door pushed open and he trailed off as you felt his eyes land on you. “Sweetheart?”

You wound your arms around your knees and pulled them into your chest. He was across the room and kneeling by your side in an instant.

“What the fuck happened, hey? Whos do I have to punch? I know yous said no more fighting, but come on, I can’t… I can’t let anyone get away with getting yous all in this state. Look at yous, doll.” His hand came to brush your hair away from your face and you flinched. “Hey, I’m not gonna hurt ya. Easy, it’s alright. Whos do I have to slap silly, hey?”

“It’s not like that…” You mumbled. “No one… If you’ve got to hit the person who made my upset you’re going to have to hit me, alright.”

“Hey now, I could never hit yous.”

“You did when we first met.

“Yeah well, I had to keep face in front of the rest of the family didn’t I? It’s not like yous didn’t hit me back anyway, but that’s not uh, don't side-track me here. Why are yous getting yourself upset?”

“I… I don’t know…” Yancy waited as you tried to find words, one of his hands stroking over your head. “Things just seem… Not that life with you isn’t great, it… you’re wonderful okay, I just… Sometimes I just feel like I’m not good at anything and I’m not going to make anything of myself and I look at other people and they’re dealing with way more shit than I am and yet here am with stupid anxious and depressive thoughts rampaging around in my brain and I just feel like… I’m useless… I would have been better off stuck in that prison…”

“Oh sweetheart…” Yancy was so gentle with you it broke your heart and you felt the first tears finally sliding free and he twisted himself and sat beside you as he pulled you in-between his legs, tucking his chin over you so your head rested on his chest. “Don’t yous be thinking like that. I wouldn’t have rescued yous unless I thought yous were someone worth saving, would I? Was a lot of work getting yous out but yous were worth every second of it. You didn’t belong in there, yous weren’t like the rest of us. So yous took some stupid box, what wes did… I’m just saying yous are worth so much than yous give yous’ credit for. There’s talent and passion in yous, and more than that, yous got a big heart. I mean, yous took me in. After all I done, yous were there… When I said I could try for parole and said when visitation was... I didn’t want to hope yous would be there, didn’t want to get disappointed. But theres yous were. Yous were there for me right, so I’m gonna for here for yous, okay?”

You clutched at his t-shirt and nodded into his chest.

“Right, good. Now yous finish up with those tears and let me see that beautiful, handsome face of yous’.” Even in this state he could make you feel shy. You wiped your thumbs under your eyes and raised your head, eyes too scared to look at him and fixated on his collarbone. “Ah theres yous is.” Yancy wiped at the wetness you’d missed smiled a shy lopsided smile. “I’m here, yous know that right?”

God he was too soft and sweet. There was apprehension in his voice, as though he was concerned you didn’t think he’d be here for you… Which wasn’t a wrong assumption, though it didn’t come from him, it just came from you not being used to have someone wanting to care for you, wanting to look after you, wanting to make sure you’re alright and be willing to listen to you and your problems… But one look at him, those big earnest eyes and the way he wore his heart on his sleeve, reassured you.

“I know,” You whispered.

“I love yous… Yous knows that too right?” His voice was so quiet and he looked down at his hands.

“Yeah, Yancy, I know. I love you too.”

His smile was blinding and instantly filled you with some warmth. Some calmness was starting to seep back in, but it would take time to feel better. But you buried your face back into his chest and you know at least he’d be by your side throughout it.

**Notes for the Chapter:**

> so yeah my head's not being that great to me right now so i wrote this because yancy's who my brain started picturing to try and help calm me down
> 
> i hope this brings some other people comfort. i'm thinking of writing more reader/yancy and reader/illinois (maybe other characters as well if people want) and adding them here as additional chapters
> 
> so feel free to send me requests/prompts/ideas/headcannons either by commenting below


	2. Yancy x Reader - First visitation

**Summary for the Chapter:**

> November 17th.
> 
> You would have never thought you’d be so happy and excited to step back in that prison, but the thought of seeing Yancy again crushed any dread you felt about the place. That last exchange you’d had through that steel gate… He’d been so gleeful as he’d led you out and then had looked to dejected when you’d asked if he was coming with you, clearly not thinking he was worth anything out in the rest of the world. But then he’d told you about visitation, he’d mentioned parole. You’d heard from the other inmates that whenever parole came around Yancy would get himself in some trouble or mess around to avoid being granted parole. He’d even said to you (or sang to you) he was praying he wouldn’t get parole. It broke your heart to think he wanted to be stuck in there forever. It broke your heart more that you couldn’t be with him. He was right, you didn’t fit in there, but you’d been missing him terribly over these last few weeks. They’d passed so slowly but now the third Sunday was finally here!

**Notes for the Chapter:**

> Anonymous asked:  
Can you do something like is the first Third Sunday and Yancy is like "nah they forgot about me" and then reader really goes to see him and what's his reaction, sorry I just need more him 😪

_November 17th._

The date stood out on the fairly plain calendar that hung on your bedroom wall, you’d circled the square containing the date vigorously in blue highlighter that was probably seeping through the shiny paper, but that didn’t matter. In fact you’d circled every third Sunday starting from the thirtieth of October onward, perhaps with the occasional hearts and stars doodled there as well.

Three weeks, three whole weeks since Yancy had single-handedly gotten you out of Happy Trails Penitentiary and if someone had asked you if you’d ever be happy to go back there you would have laughed. That someone would have probably been Mark. But he was off god knows where now. When the guards had gone through the wall to recover his injured or possibly dead body, he was nowhere to be found. You decided not to dwell on your old partner, and focused on your new friend… who maybe you wanted to be more than just a friend.

You would have never thought you’d be so happy and excited to step back in that prison, but the thought of seeing Yancy again crushed any dread you felt about the place. That last exchange you’d had through that steel gate… He’d been so gleeful as he’d led you out and then had looked to dejected when you’d asked if he was coming with you, clearly not thinking he was worth anything out in the rest of the world. But then he’d told you about visitation, he’d mentioned parole. You’d heard from the other inmates that whenever parole came around Yancy would get himself in some trouble or mess around to avoid being granted parole. He’d even said to you (or sang to you) he was praying he wouldn’t get parole. It broke your heart to think he wanted to be stuck in there forever. It broke your heart more that you couldn’t be with him. He was right, you didn’t fit in there, but you’d been missing him terribly over these last few weeks. They’d passed so slowly but now the third Sunday was finally here!

You’d already gotten everything ready and laid out the night before, you didn’t want to spend the morning fussing over what to wear or what to bring and end up being late. It felt like time whip-panned around as you got dressed, grabbed your bag and made your way to the bus stop, and in no time at all you were fidgeting and intertwining your hands in a waiting room scattered with other people visiting their friends and family and loved ones. You kept your head low under your hat but no one seemed to recognise you the slightest… you’d question it if it wasn’t far from the strangest thing that’s happened to you.

As you were all ushered through into the visitation room the realisation of what was actually happening and oh god what if he didn’t want to see you? I mean, it was a pretty stupid though, you two had become friends and you hoped started to care about each other. And he told you to come, hadn’t he? You sat down and that little bit of anxiety bubbled through you but you just focused on keeping your gaze fixed on the door.

\-----

It was visitation day, huh… Not that Yancy had been keeping track or nothing, no of course not… But he’d never really even had an inkling of when visitation day was before you came along had he? And here he was probably getting his hopes all up over nothing. God, why’d he have to be so stupid to tell you when visitation was? You were out now, in the big outside world. You could be doing all sorts of things, hell you could have moved away and hopped on the first bus away from here. It’s not like you had any reason to stay… And even if you were around, it’s not like you had any reason to remember him, you’d probably forgotten all about him by now.

Shit, he’d even thought about trying harder for parole. He wondered if you’d even heard him mumbling that he’d maybe try for parole, he’d said it so quietly with his head bowed, as if afraid to admit to himself that he was fond of you, incredibly fond of you, fond enough that he was considering giving up this prison life, this family he’d found, just to be out there with you. Not that the outside world was any more appealing… but the thought of getting to spend all his time with you, especially in a place where it was just the two of yous…

He was snapped out of his thoughts be a clanging against the bars of his cell.

“Yancy, get up,” There was a guard at his door. Why was there a guard at his door?

“Hey, what’s this about? I ain’t done nothing, I’ve been behaving myself-”

“You’ve got a visitor.”

Yancy felt like time stopped for a second. _A visitor?_ It couldn’t be you… but who else was there? Perhaps this was just done mix-up and someone had dome to visit their dear cousin Jancy and the guard has misheard… that was plausible right? Jancy was totally a name right? It felt more plausible than you actually coming back here.

He followed the guard anyway, he didn’t really have a choice, and tried not to hold his breath and hope.

\-----

You watched as a steady stream of prisoners came through the door, some of which you recognised and they looked at you with a surprised or confused look, apart from Sparkles McGee who gave you a wink and a grin and you wondered if he knew something you didn’t. Yancy hadn’t been talking about you had he? I mean… perhaps you hoped he had been. You were hoping he’d missed you as much as you’d missed him. Hell, if he’d only missed you half the amount that you’d missed him that would still be a hell of a lot.

Finally you saw him, shuffling at the back of the line, eyes staring at the ground. He seemed a mix between confused and like he just wanted to dart back to his cell. The guard poked him in the arm and then pointed at you. His eyes met yours and they widened and he blinked as if checking he really was seeing you.

“Get on over there then,” The guard prodded Yancy again, starting to push him towards you to get Yancy’s legs moving.

He slowly walked over to you in a daze and stopped at the bench opposite you across the small table. He didn’t sit down, he just kept staring at you.

“Yous… really came?” His voice sounded so small.

“Of course I did, you said visitation was every third Sunday, remember?”

“Well yeah, but I didn’t… think yous would…” He trailed off, mumbling into his chest and your heart broke.

“Yancy, why wouldn’t I come?” You tried to peer up and get a better look at his face. “Why would you think I wouldn’t come?”

“I don’t knows… There’s just a lotta stuff out there, don’t know why yous would wanna come back in here, especially if you got caught after we bust you outta here… I wouldn’t want yous getting in any trouble over me…and yous must have plenty of better things to be doing out there and I’m not…”

Oh you couldn’t bear this. He looked so forlorn and you hated that he thought you could ever forget about him. You stood up and in a few steps you were pulling him into you, wrapping your arms around his neck.

“I could never forget about you, Yancy. The best thing I can think of to do with my time, the thing I want to do the most, is spend time with you. I missed you so much.” You hoped that didn’t come off too strong but you just needed him to know that you cared.

“Missed you too, doll.” He murmured into your neck and finally seemed to relax.

You could have stayed there forever like that, but you remembered you were not the only two people in the room and you reluctantly pulled away.

“Oh, Yancy,” There was some wetness around his eyes and you brushed it away. “Come on, sit down.”

You went to walk back around the table, but he held onto the sleeve of your jacket. It seemed like he wanted to curl himself into you, the poor boy was probably touch-starved. You twisted your hand in his grip so you could link your fingers, before going to sit opposite him, pulling on his hand to get him to finally sit down and earning a laugh out of him.

You listened to him as he relayed all of the latest antics that had been happening, Bambam stabbed the newest guard, someone heard the Warden finally say ‘fuck’ (although no one knows who it was too as they all had their ears pressed against the door), and a pigeon got stuck in the mess hall for three days and they named him Ritchie.

It was hard to hear that visitation was over and you had to part ways again. Determined not to let him leave without another hug you brought him back into your arms.

“Just three more weeks, then you’ve got to deal with me again,” You smiled. “And hey, I think I’m allowed to bring you gifts, right? Anything you want? That you won’t get in trouble for having, of course.”

“Yous really don’t gotta do anything like that for me.” He smiled and shook his head.

“But I want too! I can smuggle you in sweets and books and uh…” You thought about how much he didn’t seem to want to let go of you. “How about I bring something for you to cuddle when I’m not around? If, uh, if that’s not weird…”

“S’not weird… Yous would really want to do something like that… for me?”

“Of course. I care about you, Yancy-”

“Yancy! Tell your sweetheart you’ve got to go, come on back to your cell.” The guard from the back of the room called out.

Both of you flushed at the word ‘sweetheart’ and the implication that you were his.

“Yous should probably-”

“I should probably get back-”

Both of you chuckled as you talked over each other. You were aware of your face feeling warm and god you hoped you weren’t blushing too much.

“I’ll see you in three weeks, Yancy. I’ll miss you.”

“Yeah, I’ll miss you too.”

As you left you were already making a mental list of what you could bring him as gifts. That boy was about to get some sort of stuffed animal whether he wanted one or not.

**Notes for the Chapter:**

> got my first request done! got another 14 more to get through, it's a little overwhelming but it gives me more material and inspiration for hitting that 50k for nanowrimo
> 
> and you can keep those requests coming in, i'm also taking ones for yancy x illinois because that's a thing i ship now


	3. Illnois x Reader - Sleep comfort for you both

**Summary for the Chapter:**

> "Ow," His eyes shot open as you jabbed him in the waist. He blinked up at you while you glared down at him. "Alright darlin', you caught me. I'm not keeping you awake, am I?"
> 
> "Only thing that's keeping me awake is my stupid brain. But what's keeping you awake, huh? I've never seen you having problems falling asleep. You know if you're worried about anything you can tell me."
> 
> He smiled at how earnest you were being. "It's nothing, you just try and sleep."
> 
> "It's not nothing. If you're going to lecture me about how sleep is necessary then I'll fling that right back at you."

**Notes for the Chapter:**

> credit and thank yous to people in the yancy-support-group discord server (come and join us) for giving me lots of inspiration for this:
> 
> (a collection of messages I took inspiration from)  
Starship: Illinois: .....i didn't know you where this strong sapphire  
Tinam: but Illinois exclusively using gemstones names as petnames with Y/N  
Mars: Does Illinois hold Y/N's hand when he sleeps? I feel he'd do Illi loves that Y/N has smaller hands than him  
He'll just be a blushing mess because "holy????? fuck??????? Whenever they hold hands he just has the biggest fucking heart eyes, the goofiest grin and can't stop sighing
> 
> thank you all for saying it was okay for me to take these ideas and be inspired by them and write things based on them

Sleep sometimes felt like your worst enemy.

You'd just be laying there at the end of the day all ready to rest and your body would just say no, no sleep for you. No matter how busy or active you had been that day, sleep just wouldn't happen. You'd just lay there staring at the ceiling, tossing and turning in the hope your body would find a position it liked. Laying there for who knows how long and checking the clock to realise you'd been awake for hours at that point. You could often tell when it was going to happen after about the first five minutes of laying down. You couldn't really explain it, but even if you were tired you could feel when your body and brain were just not going to accept sleep that night.

And then on the nights where insomnia wasn't holding you hostage, you'd find yourself kept away by noises and rocks digging into your back in forest shelters and caves and deserts as you stuck by Illinois side. You'd be trying to get to sleep but the slightest wind or dripping or water could keep you awake.

Not Illinois though, that man could sleep anywhere. You supposed he was used to it by now after being on so many adventures and journeys and having to sleep in all sorts of conditions and weathers and climates. He wasn't a heavy sleeper though. Though you were incredibly easily disturbed whilst trying to fall asleep, not everything woke you up once you were actually asleep. It was probably for the best Illinois wasn't a very heavy sleeper as on more than one occasion you'd been awoken by him dragging you awake (and one time giving up and you woke up slung over his shoulders) as the cave ceiling decided it didn't like you anymore and started to rain in on you both.

So he wasn't a particularly heavy sleeper, but he could fall asleep in the tightest and most uncomfortable places, which is why it was such a surprise after laying inside in your nice, warm bed with him, it had been over an hour and you knew he still wasn't asleep. Of course he hadn't said anything, he liked acting all self-sufficient and independent. It had been wonderful to watch that act fade as he got more comfortable around you and you started spending more time together and for you to realise that deep down he's soft and does care (though he still has that bravado). He's just lost so many partners he tries to push people away nonchalantly so that there's no risk of anyone else getting hurt. But you made it clear you were staying and there's no way he could get rid of you now.

You rolled off your back and onto your side to face him. He didn't move, just kept laying there with his eyes closed. You knew he was awake, his body was too tense and rigid.

"Ow," His eyes shot open as you jabbed him in the waist. He blinked up at you while you glared down at him. "Alright darlin', you caught me. I'm not keeping you awake, am I?"

"Only thing that's keeping me awake is my stupid brain. But what's keeping you awake, huh? I've never seen you having problems falling asleep. You know if you're worried about anything you can tell me."

He smiled at how earnest you were being. "It's nothing, you just try and sleep."

"It's not nothing. If you're going to lecture me about how sleep is necessary then I'll fling that right back at you."

You stayed staring at him, eyes locked as if he was challenging you to drop it. He sighed.

"It's nothing, alright. I suppose I'm just not used to all this. I'm so used to sleeping outside I hadn't realised how quiet things can get indoors. The bed's softer than what I'm used to, but it's not too bad. It's the silence I think. It's like it's just itching under my skin. But don't you worry your pretty little head about it, you can get enough beauty sleep for the two of us." And of course he winked at the end.

"Hardly," You scoffed. "I don't think I'm doing any sleeping tonight. I'd offer to open the window to help if it wasn't freezing outside."

"Now you don't have to do that on account of me. Why don't you just lie back down next to my big, strong, warm body," You laugh and drop your head onto his shoulder. "And you can at least get yourself some rest."

It was a shame you couldn't open the window though. It might help him to at least be able to hear some sounds of wind or nature or... You felt like an idiot, why didn't you think about this before?

"Now where do you think you're scampering off too?" Illinois questioned as you crawled away from him and grabbed your phone from your bedside table. "You know those things don't help you sleep right? Those screens aren't any good for you."

You ignored his complaints as you brought up Youtube on your phone. "We're not going to be looking at it, we're going to listen to it. Sometimes when I can't sleep and I'm on my own I play ASMR videos, whether it's someone talking or often just soundscapes and sound effects. The noise helps my brain focus on something that isn't my biggest worries and fears creeping into my head at the worst possible time, you know. So, I thought, there's lots of videos of forest sounds and cave sounds and nature sounds... all sorts of sounds really, and we could play one and maybe it would help?"

His brows furrowed and he looked confused for a moment before pondering whether to trust your phone.

"I'll put it face down on the table so they'll be no light and no looking at the screen," You said trying to convince him.

"Alright, if you think if might help. Can't hurt, I suppose."

You tried and not look too excited as you pulled up a video of cave sounds (water droplet effects and wind and ambience) and reached back over to put your phone back on the table, turning the volume up so he could hear it from the other side of the bed.

You laid back on your side, facing him, watching and studying him as he closed his eyes again. Ever so slowly his body started to relax into the mattress.

"So maybe your phone isn't completely evil."

"It's helping?!" You forced your voice quieter as you were too excited to be able to be helping him.

"Yeah, sapphire, it's helping," He murmured and you blushed at the pet name.

He seemed fine for a while before he began shuffling a little.

"Do you mind if I..." He glanced down at where his hand now was, stretched outwards towards you and hovering next to your own. "I just want to... know you're still here..."

Your heart ached. You were slowly working out how touch-starved he was and how long it had been for him since he'd last experienced physical affection. "Of course."

He slowly intertwined his fingers with yours, pulling your arm over his stomach as he settled your joined hands there. You nuzzled into his shoulder. His thumb stroked over the back of your hand and he chuckled.

"It's adorable how you're smaller than me," You looked up and he was just staring at your joined hands with the goofiest, softest grin on his face and he sighed and he just looked fucking _dreamy_ and you could have sworn he was blushing.

You moved to place a kiss along his jaw. "Well we can't all have 'big, strong hands' like you," You lowered your voice in some poor attempted at imitating him and you both laughed. "I'm glad though..." You muttered. "That you're fine with me and all."

"Darlin' I am so much more than 'fine' with you, you know that."

"Yeah, I know."

"And it is helping, it seems to be at least. The noise and you, holding your hand like this... sort of embarrassing to say, but of course Illinois doesn't get embarrassed by anything, but... it's nice, grounding even."

"We should do this more often then," You said around a yawn that broke out of your mouth mid-sentence.

"We should... But for now, sleep, for both of us."

You mumbled some form of agreement into his shoulder. "G'night Illy." He would groan and complain about that nickname, but he'd never actually asked you to stop using it.

"Good night, sweetheart."

**Notes for the Chapter:**

> i know it's been a little while, but my mental health took a dive but now i'm working on getting myself better.
> 
> huge thank you to everyone who's been leaving comments and kudos and requests, it means a lot.
> 
> big thanks to starship in the yancy-support-group discord server for giving me most of my inspiration for this, more on that in the notes at the top of this chapter. https://yancy-support-group.tumblr.com/


	4. Wilford x Reader -  Wilford validates you being a cute boy

**Summary for the Chapter:**

> "Yeah," You blew out a laugh. "I was thinking about me... being a boy and all, and I just... I felt like looking cute."
> 
> "Okay...?" He blinked down at you and cocked his head to the side. "Am I missing something?"
> 
> "Well... I'm a boy, I'm male, people already look at me and don't see a boy and now I want to dress in cute colours and stuff and so that makes it kind of definitive that no one will see me as male, because I won't look masculine enough..."

**Notes for the Chapter:**

> trans-male!/genderfluid! reader + trans! wilford

Gender was frustrating.

There were so many rules and expectations being put on how you had to act if you were a boy or a girl, and then if you weren't either if you still had to be masculine or feminine or if you weren't allowed to be either. It was so stupid. You knew you were a boy, you _knew_ you were... It was just hard to think that when you were just in such a mood to be, well, cute. You just wanted to throw on something baby blue or pink, some pride wristbands, hell if you were feeling incredibly brave and carefree maybe even a skirt, maybe even make-up? Perhaps not that much but, you couldn't explain why but you just wanted to look cute.

But that wasn't allowed, was it? You're identifying as male, so therefore you should have to want to be masculine? If anyone else told you they were feeling that way you'd tell them of course not, being a boy isn't about feeling or wanting to be masculine, and being a girl isn't about feeling or wanting to be feminine... But you're not talking to someone else... you're talking to you and that advice just feels stale on your tongue when you apply it to yourself.

You stood looking at yourself in the mirror. It'd be so easy to just grab something out of your wardrobe, it's not like you didn't own cute and pastel clothes. Wilford had bought some of them for you (he liked you to match colours sometimes, it was adorable) and some of them were from before... before you realised your gender, and you still thought they were cute. It would be so easy just to not care whether anyone else thought you were male... It's not like you were planning on even going out anywhere, you just at least wanted to feel nice inside your own home but...

"You in here, sugarplum?"

Oh no Wilford was back and he was going to see you getting all worked up.

"You okay?" He stopped in the doorway, squinting at you and looking you up and down. "You're just sorta... standing there."

"It's nothing, Will," You bit your lip and turned away from the mirror.

"Now, don't give me that, look at you. What is it?" He demeanor shifted. "Did someone hurt you?" You could feel the danger radiating off him.

"No, no, it's nothing like that," You reach out to touch him, your palms sliding on his chest. Physical contact always seemed to calm him down and ground him. "I just... I was thinking..."

"Ah, well, that's a dangerous thing to be doing."

"Yeah," You blew out a laugh. "I was thinking about me... being a boy and all, and I just... I felt like looking cute."

"Okay...?" He blinked down at you and cocked his head to the side. "Am I missing something?"

"Well... I'm a boy, I'm male, people already look at me and don't see a boy and now I want to dress in cute colours and stuff and so that makes it kind of definitive that no one will see me as male, because I won't look masculine enough..."

You bowed your head and didn't look up at Wilford. He didn't go into stoic silences often and you could feel your anxiety churning in your gut.

"Sweetness, you do know who you're talking to right? Look at me," You didn't move and he tilted your chin. "Am I at all stereotypically masculine?"

You looked at him. There was still pink hair dye lingering at the ends of his hair, which was flopping into his right eye, and covering meticulously maintained moustache. He had a pink button-up shirt rather than his usual yellow, with suspenders that bore the trans pride flag colours in their stripes connecting to pale blue trousers. He almost ruined the look by wearing those ridiculous, pink crocs.

"Okay so... not typically masculine colours, but you look good in them. You still like... The way you carry yourself and your voice and everything," You insisted.

"Well, as flattered as I am, that all took time you know, I'm sure you could master it if you worked at it, but just because you think I'm... passing better than you, doesn't mean you're doing it wrong. There's no wrong way to be you," He stroked his hands over your head. "Who are you trying to convince, hm? Who's opinion is bothering you? Because I'll have you know, cupcake, most people are idiots so it really doesn't matter what they think."

You buried your head into his shirt. "Was worried about what you'd think," You mumbled into the fabric.

Suddenly there were hands on your shoulders, pushing you back so that Wilford could see all of you. "What nonsense are you coming out with now? Why would it matter in the slightest to me?"

You looked at the floor. "Because you're hardly going to see me as your boyfriend if I look like a girl." You shifted your weight, you were not going to cry.

"Since when does wearing pink make you a girl? And even if the point is you want to look girly or feminine, why would you think that I...? You know we're in the same boat, sugar, but do I look like I'm letting what clothing people think is 'masculine' stopping me from wearing whatever I feel like?"

You shook you head.

"Right," His hands left you. "What do we have then?"

You looked up and he was rummaging through your wardrobe.

"What are you doing?" You asked.

"Finding you something cute to wear. You'll look absolutely, delectably, adorable." He turned and grinned at you and you finally started feeling more at ease as a blush tinted your cheeks.

Some of Wilford's fashion choices baffled you, but at least he knew what colours went together. There wasn't that many pieces to go through, and he held each one up to you, turning his head this way and that way, checking with you if you were comfortable wearing each item. Seeing as you didn't feel confident enough to go out he decided on something comfortable and lazy, a pair of pale pink leggings and an oversized white sweater that had a rainbow pastel rainbow stripe stretching from just under one armpit to the other. It buried you when you put it on and Wilford made the most ridiculous 'aww' or cooing sound which he assured to be because he was just so besotted with how sweet you looked.

"The finishing touch," He said as his hands brushed around your neck and he fastened on a baby pink choker. It had a metal charm of a flower, with pink stones in the petals and a white one in the centre, dangling from the centre just above the hollow of your throat. "Do you feel as cute as you look, honeybun?"

Your face heated up at the pet name, it always did every time he used one, and you managed to get yourself to nod. It was a pretty cute outfit, there was just still that worry of looking like a boy. You told yourself Wilford was right, it just mattered what you felt like not what you looked like, and he'd know, he'd been down this road just as you had.

"What do _you_ think?" You asked tentatively, but smiling as you already knew the answer unless it had changed from the compliments he'd been giving you seconds ago."

"I think that I am incredibly lucky to have such a cute boyfriend," He leaned around to plant a kiss on your cheek, moustache tickling your skin. "I think I'm going to have to dress you up more often."

You think you'd let him as well.

**Notes for the Chapter:**

> something completely self-indulgent because i needed to hear this said to me because i'm worrying a lot about it
> 
> basically i wanna feel cute today but still be a guy and i think the ultimate 'you can be a guy and wear cute shit and pink and not be crazy masculine' advocate is wilford
> 
> so listening to kirby music playlists and 'in love with a ghost' is a total mood for being in this headspace of wanting to feel cute, but also being around wilford. could super recommend [ ｃｈｉｌｌ ｗｉｔｈ ｋｉｒｂ ~ 【ｌｏｆｉ ｍｉｘ カービーミックス】](https://www.youtube.com/watch?v=fDKOLx66eVg)

**Author's Note:**

> feel free to send me requests/prompts/ideas/headcannons either by commenting below or in my ask box on tumblr


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